Coumaranone → Benzofuran-3-acetonitrile

HRID 22926

反応式

HRID 22926 の反応式
[H-].[Na+].CCOP(OCC)([CH2:8][C:9]#[N:10])=O.[O:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=O)[CH2:15]1>C1COCC1.CCOC(C)=O.O>[O:14]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]([CH2:8][C:9]#[N:10])=[CH:15]1

参加物

7

反応物 3

HCID 23556CoumaranoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

生成物 1

HCID 2769401Benzofuran-3-acetonitrile収率 91%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride (268 mg, 6.7 mmol) was slurried in dry THF (10 ml) at 0° C. under nitrogen and diethyl cyanomethyl phosphonate (1.1 ml, 6.7 mmol) added dropwise and the whole stirred for 45 min. 3-Coumaranone (Lancaster) (900 mg, 6.7 mmol) was then added dropwise and the whole stirred at room temperature for 45 min. The reaction was diluted with EtOAc (15 ml) and water (15 ml), and the organic layer was then separated, dried (MgSO4) and evaporated and the residue flash chromatographed using 0-5% EtOAc in pentane to give the title product (940 mg, 91%); 1HNMR (400 MHz, CDCl3) δ: 3.77 (s, 2H), 7.25-7.40 (m, 2H), 7.52 (dd, 1H), 7.58 (dd, 1H), 7.67 (s, 1H); LRMS: M+NH4+, 175. (TS+).

後処理

  1. stirringthe whole stirred at room temperature for 45 min
  2. customthe organic layer was then separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe residue flash chromatographed

出典と根拠

ORDレコード
ord-2f6af7b148ca4b5fbdfe0f4a8c622d38
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

関連ノート

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